However, the world is going digital whether you like or not. Look at cars from the 60s and now. The modern cars have less easily serviceable parts than back then. That doesn't mean that people don't appreciate classic cars... Its just that modern cars, are now easier to use and generally less problematic. I remember as a youngster, getting into a car and there was a strong possibility that you wouldn't get to your final destination... or you would be nervously looking at the temperature gauge if you were stuck in a traffic jam.
With regard to digital pedals, I have never seen, or known a pedal crash - can anybody else comment on this being an occurrence? Maybe the more comprehensive units - but from memory, they are down to users trying beta firmware and the like - and obviously running code in beta should come with certain caveats!
Digital gear can go obsolete... but you know what, the Kemper profiler was unveiled in 2011 - that's pretty impressive that it's still competitive in the marketplace and there's still capacity for the DSP to be continued to be improved. The Kemper profiler is an amazing example of having a road map and despite the ageing technology, it's still capable to keep up - and even exceed - the offerings offered by their competitors.
In reality, choice is a beautiful thing. We have analogue. We have digital. Great. Knock yourself out. And I know that this may be crazy talk... but digital and analogue can co-exist. For now.
One last thing, there are analogue stompboxes that still sound great but have some terrible traits... like being super noisy, or suck all your tone, or don't bypass nicely. I know that some of these problems can be fixed (e.g. loopers and the like)... but the truth is, there are some pedals that have some sort of mystical quality because of who used them... but as a pedal in themselves, they do kinda suck. The Mutron comes to mind. Sounds great - but oh so noisy.
As for older digital pedals... well, there are a few notable exceptions. The Deep Impact, ME8B maybe...